Environmentally Friendly Organic Chemistry Laboratory Experiments for the Undergraduate Curriculum: A Literature Survey and Assessment

Mohan, Ram S.; Mejia, Maria P.

doi:10.1021/acs.jchemed.9b00753

Cited by 13 publications

(17 citation statements)

References 75 publications

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“…The modern emphasis on green chemistry and sustainability in undergraduate organic chemistry curricula has resulted in an increasing number of supplemental discussions and oxidation experiments for instructional organic chemistry laboratories that feature green chemistry aspects . Alternative protocols to the classical Jones- or Corey-Suggs-type oxidations involve the use of bleach as an oxidant, but this results in a disconnect between the lecture–laboratory dynamic and further does not alleviate the “categorical” approach many students take to redox processes.…”

Section: Introductionmentioning

confidence: 99%

“…In addition to being advantageous pedagogically, Bobbitt’s salt has many of the desirable attributes discussed by prior “green” undergraduate experiments. − The reagent itself is derived from 4-amino-2,2,6,6-tetramethylpiperidine (a cheap tetramethylpiperidinyl variant produced from acetone and ammonia) and can be prepared in aqueous media. , It has been commercialized and can be purchased from an array of vendors (at ∼$6 per gram) or prepared in house (∼$0.50 per gram) . The physical properties of the oxidant make it an ideal reagent for the undergraduate laboratory setting.…”

Section: Introductionmentioning

confidence: 99%

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A Practical Oxidation Experiment for Undergraduate Students: Bobbitt’s Salt as a “Green” Alternative

et al. 2022

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Oxidation reactions are critical components of the synthetic toolbox taught to undergraduate students during introductory organic chemistry courses. However, the oxidation reactions discussed in the undergraduate curriculum are often outdated as many organic chemistry textbooks emphasize chromium-based oxidants that are no longer in regular use by practitioners, which may limit an instructor’s time to allocate to discussion of other oxidants. Further, laboratory courses have since either removed oxidation experiments or replaced them with oxidative processes not discussed in lectures, thus leading to a disconnect between the two learning settings. As part of an effort to bridge this divide and modernize the oxidation reactions discussed in our curricula, we have developed a new laboratory experiment that uses a commercially available oxoammonium salt (Bobbitt’s salt) to cleanly oxidize cinnamyl alcohol to cinnamaldehyde. In addition to being a safe, convenient, colorimetric, and “green oxidant” suitable for use in the undergraduate teaching laboratory, the hydride-transfer mechanism allows for overlap with key course concepts presented in both introductory and advanced lecture courses. The procedure is well-suited for small and large organic I, II, or advanced laboratory sections alike and can be completed within a standard 3–4 h laboratory period. Aside from exposing students to a modern green oxidation protocol, the experiment contains expanded opportunities for interpretation of 1H NMR, 13C NMR, and IR spectra. An optional addendum for advanced students involving Hammett correlations was also developed.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A Practical Oxidation Experiment for Undergraduate Students: Bobbitt’s Salt as a “Green” Alternative

et al. 2022

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“…The mechanochemical methods are currently successfully used in chemical education to demonstrate the benefits of solvent-free organic ,− and inorganic , syntheses, as well as the foundations of solid-state chemistry , to students. It has been noted , that students and educators can employ mechanochemical methods to demonstrate distinct facets of eco-friendly chemical transformations (the low-energy inputs, the absence of toxic reagents or solvents, fewer synthesis or purification steps in some cases, etc.).…”

Section: Introductionmentioning

confidence: 99%

Introducing Students to Energy-Efficient Mechanochemistry of Biopolymers

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Matveeva

2022

J. Chem. Educ.

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A comprehensive laboratory work that allows students to gain hands-on skills in energy-efficient mechanochemistry is described. Standard university curricula are paying very little attention to mechanochemistry, although skills in this discipline are highly demanded among chemistry graduates. In this study, a comprehensive description of mechanical destruction of α-cellulose was chosen as a model task for students to perform. The structure of cellulose is best suitable for demonstrating the effects occurring upon mechanical treatment. While being sufficiently complex (as it is characterized by high molecular weight and the presence of crystalline and amorphous regions), cellulose is simultaneously rather simple (as it consists of glucose units only and contains no branching) and allows one to consider rupturing of a macromolecule chain as the only possible mechanochemical reaction. This study employs the view commonly held in mechanochemistry that the field of mechanical forces undergoes relaxation through the following pathways: heating of the system, grinding of material, amorphization of the crystalline structure, and occurrence of mechanochemical reactions. This multilevel investigation of the process according to the "bottom up" approach has allowed the students to identify the relaxation pathways through which energy is expended during treatment of amorphous/crystalline biopolymers. It is safe to say that this approach allows the new generation of chemists not only to routinely assess and enhance the energy efficiency of the existing technologies but also to develop novel technologies employing hardly accessible and nonreactive substances.

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“…Readers of the Journal recognize the popularity of EAS reactions. Creative variations abound, including an emphasis on green chemistry, − physical organic chemistry, − medicinal chemistry, − polymer matrix chemistry, reactions with unusual nucleophiles (azulene, ferrocene) and electrophiles (a protonated ketone, the tropylium cation, an anhydride), − an intramolecular reaction, and reactions highlighting the environmental impact of industrially important chemicals . Some of these offerings include computational exercises in which students investigate relative reactivities and product distributions; others incorporate EAS in a multistep reaction sequence.…”

Section: Introductionmentioning

confidence: 99%

Expanding the Scope of an Electrophilic Aromatic Substitution Discovery Experiment Including Hydride and Methyl Shifts

et al. 2021

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Friedel–Crafts alkylation reactions using a curated set of alcohols provide students with the opportunity to combine the study of electrophilic aromatic substitution with carbocation rearrangements. In this experiment students may be presented with up to nine alcohols that yield six products, all synthesized under identical reaction conditions. They distinguish their products using a range of instrumental methods including infrared, 1H NMR, and 13C NMR spectroscopies, and mass spectrometry. Additional characterization is provided by the determination of melting point/mixed-melting point and gas chromatographic retention time. Students work in teams to assign structures to their individual reaction products; providing nine starting materials ensures minimal duplicates in a given laboratory section. As students interpret their data, some discover that a carbocation rearrangement occurred, resulting in isolation of only one product despite starting from a pair of isomeric reagents. This laboratory provides students with the opportunity to engage in a range of laboratory and problem-solving skills, and thus is designed to be performed toward the end of a two-semester organic chemistry sequence.

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Environmentally Friendly Organic Chemistry Laboratory Experiments for the Undergraduate Curriculum: A Literature Survey and Assessment

Cited by 13 publications

References 75 publications

A Practical Oxidation Experiment for Undergraduate Students: Bobbitt’s Salt as a “Green” Alternative

A Practical Oxidation Experiment for Undergraduate Students: Bobbitt’s Salt as a “Green” Alternative

Introducing Students to Energy-Efficient Mechanochemistry of Biopolymers

Expanding the Scope of an Electrophilic Aromatic Substitution Discovery Experiment Including Hydride and Methyl Shifts

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